You would want to holistically look at your personal balance sheet for sources of liquidity and credit (cash, brokerage account, credit card, HELOC, 401k borrowing capacity, Roth IRA contributions, etc.).  

capital gains vs. self employment/regular income2- Would the income of the sale of the flip be looked at holistically along with the expenses of my other rental properties?

Once you've done those things, you should have a holistic view of the MTR market.

You say "It is not worth the hassle", which I also see others express who have not holistically looked at a persons overall financial situation.

Any guidance or advice from someone that understands not only RED but with a holistic and sustainable approach to the whole process, materials, Net Zero, Passive H design, etc.

I’m thinking holistically about the move, and how I can get started in real estate in either market.

Of course I assume the parents consulted their legal and tax advisors and determined gifting was the appropriate path to meet their goals while minimizing the holistic tax on the family.

If it's a commercial lender, they will typically look at everything holistically, but a main driver will be ensuring the new deal hits their DSCR requirements.  

Kudos to Bill Gulley and numerous others on this thread for sharing their experiences that gives me a more holistic view of real estate investing, despite them possibly not agreeing 100% on everything.

Holistic view of your personal balance sheet.